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High Throughput Determination of Ammonium and Primary Amine

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High Throughput Determination of Ammonium and Primary Amine High throughput determination of ammonium and primary amine compounds in environmental and food samples Fabien Robert-Peillard, Edwin Palacio, Marco Ciulu, Carine Demelas, Frédéric Théraulaz, Jean Luc Boudenne, Bruno Coulomb To cite this version: Fabien Robert-Peillard, Edwin Palacio, Marco Ciulu, Carine Demelas, Frédéric Théraulaz, et al.. High throughput determination of ammonium and primary amine compounds in environmental and food samples. Microchemical Journal, Elsevier, 2017, 133, pp.216-221. 10.1016/j.microc.2017.03.048. hal-01499481 HAL Id: hal-01499481 https://hal-amu.archives-ouvertes.fr/hal-01499481 Submitted on 18 Apr 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. High throughput determination of ammonium and primary amine compounds in environmental and food samples F. Robert-Peillard1, E. Palacio Barco2, M. Ciulu1, C. Demelas1, F. Théraulaz1, J.-L. Boudenne1, B. Coulomb1 1 Aix Marseille Univ, CNRS, LCE UMR7376, 13331 Marseille, France. 2 Laboratory of Environmental Analytical Chemistry. University of the Balearic Islands, E- 07122 Palma de Mallorca, Illes Balears, Spain. SUPPLEMENTARY INFORMATION 12000 (a.u.) 10000 Intensity 8000 6000 4000 Fluorescnce 2000 0 8.8 9 9.2 9.4 9.6pH 9.8 10 10.2 10.4 10.6 Borate Carbonate CAPS + Sup. Fig. 1: Influence of buffer. [OPA]: 8 mM; [NAC]: 8 mM; [NH4 ]: 100 µM; pH = 10.5 1 High throughput determination of ammonium and primary amine compounds in 2 environmental and food samples 3 4 Fabien Robert-Peillard1*, Edwin Palacio Barco2, Marco Ciulu1, Carine Demelas1, Frédéric 5 Théraulaz1, Jean-Luc Boudenne1, Bruno Coulomb1 6 7 1 Aix Marseille Univ, CNRS, LCE UMR7376, 13331 Marseille, France. 8 2 Laboratory of Environmental Analytical Chemistry. University of the Balearic Islands, E- 9 07122 Palma de Mallorca, Illes Balears, Spain. 10 *Corresponding author: [email protected] 11 12 Abstract 13 In this paper, an improved spectrofluorimetric method for the simultaneous and direct 14 determination of ammonium and primary amine compounds is presented. The method is 15 based on the derivatization with o-phthaldialdehyde (OPA) / N-acetylcysteine (NAC) reagent 16 using high throughput microplates, and OPA/NAC ratio has been optimized in order to 17 suppress interference of ammonium on primary amine determination. Direct measurement of 18 these two parameters is therefore possible with a global procedure time that does not exceed 19 ten minutes. Excellent limits of detection of 1.32 µM and 0.55 µM have been achieved for 20 ammonium and primary amines, respectively. Reagent stability issues have also been 21 addressed and formulation of reagents solution is described for improved reagents shelf life. 22 The proposed protocol was finally applied and validated on real samples such as wine 23 samples, compost extracts and wastewater. 24 25 Keywords: ammonium; primary amine; microplate; reagents stability. 26 27 1. Introduction 28 Amino compounds are widely distributed in the environment and essentially result from 29 metabolic processes of degradation, hydrolysis and excretion at different levels of the food 30 chains. Soil organic matter thus contains about 30% of its nitrogen pool as amino acids [1], + 31 and a significant proportion of NH4 can be released from organic matter by microbial 32 hydrolysis [2]. Anthropogenic activities also contribute to the presence of these compounds 33 and ammonium in the environment, mainly attributed to the incineration of waste [3] and the 34 discharges of waste waters from chemical industry and wastewater treatment plants [3,4]. 35 Among the nitrogen pool, primary amino compounds determination is a significant parameter 36 in the food processing or drinking-water treatment industry as it can react with nitrites or 37 nitrates to form nitrosamines which are classified as "probably carcinogenic to human" [5,6]. 38 Primary amino compounds (mainly primary amino acids) are also very important regarding 39 the nitrogen management in some specific fields such as wine industry [7]. Indeed, assaying 40 the total primary amino acids concentration is often considered to be the most convenient 41 method to measure assimilable nitrogen, which is critical for wine flavour and style. 42 Regarding ammonium, its determination in environmental samples is highly relevant, due to 43 its important micronutrient function in aquatic systems or as an important index in 44 composting process studies. As example, high concentration in a water body can be an 45 indicator of the environmental impact of human activities, with strong effects on 46 microbiological activities that can potentially lead to eutrophication events [8]. In the + - 47 composting field, low ammonium concentration coupled to low N-NH4 /N-NO3 ratio has 48 been proposed as indicators of a compost stability [9]. 49 Several methods have been proposed for the analysis of ammonium [10], such as 50 spectrophotometry [11,12,13], ion selective electrode [14], fluorimetry [15,16] or ion 51 chromatography [17]. Primary amines/amino acids are generally analyzed individually by 52 liquid chromatography [18,19], but methods have also been developed to measure the total 53 concentrations of these compounds in order to have a rapid and global assay of these 54 important nitrogen compounds. This can be done for example by spectrophotometric 55 measurements after reaction with ninhydrin [20] or by fluorimetry after reaction with o- 56 phthaldialdehyde (OPA) and a thiol compound [21]. 57 The numerous advantages of the combination of this OPA-thiol reagent (reaction with 58 ammonium and amines, sensitivity, selectivity, low toxicity and price of reagents...) has led to 59 the development of simultaneous determination methods for ammonium and primary amino 60 compounds. Meseguer Lloret et al.[14] used solution derivatization with OPA-NAC reagent 61 (NAC: N-acetylcysteine), two different excitation and emission fluorescence wavelengths and 62 statistical analysis by multivariate Principal Component Regression in order to separate the 63 responses of ammonium and amine under selected experimental conditions [15]. Darrouzet- 64 Nardi et al. [22] developed a fluorescent assay with OPA and β-mercaptoethanol for analysis 65 of primary amino compounds, by taking into account potential interference of ammonium. 66 The main drawback of this method was the necessity to use a 1-h incubation time in order to 67 reduce interference from ammonium. 68 The aim of the present study is to develop a fast, simple and efficient method for ammonium 69 and primary amino compounds analysis, with no need of statistical analysis, direct 70 measurement from calibration curves and a global procedure time that does not exceed ten 71 minutes. Moreover, this method has been developed as a potential routine analytical method 72 applicable to the large number of samples that an analytical laboratory typically has to deal 73 with (especially for ammonium). Therefore, a high-throughput microplate method based on 74 OPA-NAC reagent was used, with special care on reagents stability which is a key point for 75 routine analysis development (shelf life of at least 3 months without deterioration of analytical 76 performances). The final goal of this study was to conduct a strong validation on complex 77 samples like compost extracts or wastewaters by comparison with a chromatographic 78 reference method, in order to have a robust method for routine analysis of ammonium and 79 primary amino compounds. 80 81 2. Experimental 82 2.1 Reagents and solutions 83 All chemicals were of analytical reagent grade and used without further purification. OPA 84 was obtained from Acros Organics and N-acetyl-L-cysteine (NAC) and tris(2-carboxyethyl) 85 phosphine hydrochloride (TCEP) from Sigma-Aldrich. OPA solutions were prepared by 86 dissolving pure compound in appropriate buffer and adjusted at pH=10.5 with sodium 87 hydroxide or hydrochloric acid. CAPS, borate and carbonate buffers were prepared by 88 dissolving N-cyclohexyl-3-aminopropanesulfonic acid (Acros Organics), sodium tetraborate 89 decahydrate (Sigma-Aldrich) and anhydrous sodium carbonate (Sigma-Aldrich) respectively 90 in ultrapure water (Millipore, resistivity >18 MΩ cm). Stock solutions of individual amino 91 compounds (10 mM each) were prepared by dissolving appropriate amounts of pure 92 compound (Sigma-Aldrich) in ultrapure water. Stock standard ammonium solution (55.5 mM) 93 was prepared by dissolving appropriate amount of ammonium chloride in deionized water. 94 Working solutions were obtained by diluting stock solutions to proper concentrations. 95 96 2.2 Instruments 97 2.2.1 Microplate 98 Microplate fluorescence measurements were carried out on a microplate reader (Infinite 99 M200, Tecan France SAS, Lyon, France), operated at 30 °C and controlled by i-control™ 100 software (Tecan). Detection was performed by top fluorescence reading at λex = 335 nm and 101 λem = 455 nm for total primary amines quantification and at λex = 415 nm and λem = 485 nm 102 for ammonium determination. Other parameters were as follows: gain: 80; number of flashes: 103 5; integration time: 20 µs. Fluorescence intensities were expressed in arbitrary units (a.u.). 104 Polystyrene black 96 V-well microplates (Fisher Scientific, Illkirch, France) were used. 105 106 2.2.2 Ion chromatography analysis of ammonium 107 The ion chromatographic system consisted of an IonPac CS12A 4x250 mm column 108 (ThermoScientific), a CSRS-Ultra 4 mm self-regenerating suppressor, an AS40 auto-sampler, 109 an ED40 electrochemical detector operated in the conductivity mode and a GP40 gradient 110 pump operating at a flow-rate of 1.0 mL/min (Dionex). The injection loop was 50 μl.
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